Benzylamine → HCID 78323676, compound

Participants

Reaction Steps

5-(4-Hydroxy-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide (0.100 g, 0.272 mmol) was dissolved in THF (10 mL) and BOP reagent (0.181 g, 0.408 mmol) and DIPEA (0.143 mL, 0.817 mmol) were added. The reaction mixture was stirred at room temperature for 30 min. Benzylamine (0.0440 g, 0.408 mmol) in THF (3 mL) was added and the reaction mixture was stirred at room temperature for 14 h. The reaction mixture was concentrated under reduced pressure and water was added (30 mL). The resulting aqueous solution was extracted with ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by prep HPLC (Condition B-61 as described in general methods) to obtain 5-(4-(benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide (0.0250 g, 20.1%). LCMS Condition B-38: retention time 2.08 min, [M+1]=457.2. HPLC Condition B-5: retention time 20.11 min, Purity 97.00%. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.84 (d, J=5.6 Hz, 2H), 6.76 (t, J=5.6 Hz, 1H), 6.84 (d, J=2.8 Hz, 1H), 7.30 (t, J=7.2 Hz, 1H), 7.34 (t, J=7.6 Hz, 2H), 7.40-7.45 (m, 3H), 7.48 (t, J=7.6 Hz, 2H), 7.55 (dd, J=1.6, J=3.4 Hz, 2H), 7.68 (br s, 2H), 7.95 (d, J=2.4 Hz, 1H), 8.94 (t, J=2.2 Hz, 1H), 9.05 (d, J=2.4 Hz, 1H), 9.53 (d, J=1.6 Hz, 1H).

Provenance & Evidence